diff --git a/src/math.ts b/src/math.ts
index 5b8f119fc..50faf886a 100644
--- a/src/math.ts
+++ b/src/math.ts
@@ -52,3 +52,45 @@ export function rotate(
     (x1 - x2) * Math.sin(angle) + (y1 - y2) * Math.cos(angle) + y2
   ];
 }
+
+interface Line {
+  x1: number;
+  x2: number;
+  y1: number;
+  y2: number;
+}
+
+interface Point {
+  x: number;
+  y: number;
+}
+
+const vcp = (a: Point, b: Point) => {
+  return a.x * b.y - a.y * b.x;
+};
+
+//https://stackoverflow.com/a/565282/816116
+export const testLineSegmentIntersect = (l1: Line, l2: Line) => {
+  const r: Point = { x: l1.x2 - l1.x1, y: l1.y2 - l1.y1 };
+  const s: Point = { x: l2.x2 - l2.x1, y: l2.y2 - l2.y1 };
+
+  // r x s
+  const div = vcp(r, s);
+
+  // q - p
+  const sub = { x: l2.x1 - l1.x1, y: l2.y1 - l1.y1 };
+
+  // t = (q - p) x s / (r x s)
+  const t = vcp(sub, s) / div;
+
+  // u = (q - p) x r / (r x s)
+  const u = vcp(sub, r) / div;
+
+  if (div === 0 && vcp(sub, s) === 0) {
+    return true;
+  } else if (div !== 0 && t >= 0 && t <= 1 && u >= 0 && u <= 1) {
+    return true;
+  }
+
+  return false;
+};
diff --git a/src/scene/selection.ts b/src/scene/selection.ts
index b1fbc13ee..9db217895 100644
--- a/src/scene/selection.ts
+++ b/src/scene/selection.ts
@@ -1,5 +1,6 @@
 import { ExcalidrawElement } from "../element/types";
 import { getElementAbsoluteCoords } from "../element";
+import { testLineSegmentIntersect } from "../math";
 
 export function setSelection(
   elements: ExcalidrawElement[],
@@ -18,12 +19,70 @@ export function setSelection(
       elementX2,
       elementY2
     ] = getElementAbsoluteCoords(element);
-    element.isSelected =
-      element.type !== "selection" &&
-      selectionX1 <= elementX1 &&
-      selectionY1 <= elementY1 &&
-      selectionX2 >= elementX2 &&
-      selectionY2 >= elementY2;
+    if (element.type === "selection") {
+      element.isSelected = false;
+    } else if (element.type === "arrow") {
+      if (
+        selectionX1 < elementX1 &&
+        selectionX2 > elementX2 &&
+        selectionY1 < elementY1 &&
+        selectionY2 > elementY2
+      ) {
+        element.isSelected = true;
+      } else {
+        // lt -> lb
+        const line1 = {
+          x1: selectionX1,
+          y1: selectionY1,
+          x2: selectionX1,
+          y2: selectionY2
+        };
+
+        // rt -> rb
+        const line2 = {
+          x1: selectionX2,
+          y1: selectionY1,
+          x2: selectionX2,
+          y2: selectionY2
+        };
+
+        // lt -> rt
+        const line3 = {
+          x1: selectionX1,
+          y1: selectionY1,
+          x2: selectionX2,
+          y2: selectionY1
+        };
+
+        // lb -> rb
+        const line4 = {
+          x1: selectionX1,
+          y1: selectionY2,
+          x2: selectionX2,
+          y2: selectionY2
+        };
+
+        const target = {
+          x1: elementX1,
+          y1: elementY1,
+          x2: elementX2,
+          y2: elementY2
+        };
+
+        element.isSelected =
+          testLineSegmentIntersect(line1, target) ||
+          testLineSegmentIntersect(line2, target) ||
+          testLineSegmentIntersect(line3, target) ||
+          testLineSegmentIntersect(line4, target);
+      }
+    } else {
+      element.isSelected = !(
+        (selectionX1 < elementX1 && selectionX2 < elementX1) ||
+        (selectionX1 > elementX2 && selectionX2 > elementX2) ||
+        (selectionY1 < elementY1 && selectionY2 < elementY1) ||
+        (selectionY1 > elementY2 && selectionY2 > elementY2)
+      );
+    }
   });
 }